If you had to choose one tool that defined Adobe Illustrator, it would undoubtedly be the Pen tool. Illustrator is known primarily for its ability to produce high-quality illustrations, reproducible at any resolution. The vector paths created by the Pen tool are completely flexible and, because they are vectors rather than pixels, never degrade no matter the resolution. Unfortunately, the Pen tool is one of the hardest to master; however, with a bit of practice, you’ll find yourself beginning to draw the most sophisticated of shapes.

One technique for learning how to use the Pen tool stems from a common early childhood practice: tracing. Chances are you’re like me and millions of other children who spent hours outlining their favorite animal, flower, or character with a carefully selected crayon—perhaps, like me, with your tongue stuck out of the side of your mouth in deep concentration. In the upcoming exercise, you’ll have an opportunity to relive those days, but with the Illustrator Pen tool instead of a crayon: Whether your tongue sneaks out or not is up to you.

1- Open Adobe Illustrator and, from the Workspace Switcher, make sure Essentials is chosen. Almost all the available workspaces keep the tools you’ll need in this exercise front and center, but the Essentials option is the default.

Note: While it is true that Illustrator has a very robust tracing feature called Live Trace, using it won’t give you the practice you’ll need to master the Pen tool. However, if you’d like to experiment with this feature, select the JPEG image and, from the Options bar, click Live Trace. There are a good number of presets from which to choose on the left side of the Live Trace Options bar that can give you a sense of what’s possible.

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From the Tools panel, click Fill, the large white color swatch near the bottom of the panel.

When you click Fill, the Color panel expands from the docked panel group on the right of the workspace.

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In the Color panel, choose No Color, the white block with the red line through it, located on the far left side of the gradient. When you’re done, close the Color panel.

Because the goal here is to initially trace the outside of the hummingbird, it’s best to turn the fill off. If you don’t, Illustrator completes the fill for any plotted points as you move your Pen tool from place to place, which can lead to irrelevant masking shapes.

5 - From the Tools panel, choose the Pen tool, the first icon in the second group.

Notice that the cursor changes to a pen with a small x on the right side. Illustrator uses this symbol to indicate that it is ready to start a new path. Throughout this exercise, I’ll point out other symbols and the Pen tool mode they signify.

6 -
Press Ctrl++ (Windows) or Command++ (Mac) four times to zoom in to a 400% magnification. Press the space bar and drag the image so that the bird’s head is visible. From the View menu, choose Smart Guides to toggle them off.

Smart Guides in Illustrator, as you’ve seen in Photoshop and Fireworks, are great for positioning elements. However, when drawing with the Pen tool, they can get in the way and I find it best to work without them, at a higher magnification.

7 -
Place your cursor at the very tip of the hummingbird’s beak, click once, and drag slightly to the upper right.

Now that you’ve begun to work with the Pen tool, I can let you in on a secret: You don’t really draw vector paths with the Pen tool; you plot anchor points, and Illustrator draws the paths. The Pen tool creates two types of anchor points:Corner anchor points—Used to draw straight lines by clicking once.Smooth anchor points—Used to draw curved lines by clicking and dragging; two handles (called direction handles, also known as Bézier handles) control the shape of the curve.

You’ve just created a smooth anchor point. Notice that the cursor now shows a pen icon without an x or any other symbol in the lower right; this indicates that the Pen tool is in the process of drawing a path. Now you’ll create another smooth anchor point and Illustrator will draw a slightly curved line connecting the two.

Place your cursor on the top part of the beak about 2/3 the way to the eye. Click, press Shift, and drag to the left until the line between the two points matches the curve of the beak.

Press Shift when you want to constrain the Pen to a horizontal or vertical direction handle. I’ve found that handles set at 90 degrees often make it easier to get symmetrical curves.

Note: Just as you can press the space bar to temporarily switch to the Hand tool and move the document, you can also use it if you need to move a just-added anchor point. If you realize you are positioning the anchor point incorrectly, keep your mouse button pressed and press Space: You’ll then be able to move the anchor point to any new location.

9 - Place your cursor on the right side of the bird’s skull, in line with the top of the eye. Click, press Shift, and drag up until the connecting line matches the curve of the head.

Because of the curved nature of the bird’s head and the placement of the previous point, you just need one more point to draw the line around the skull.

10 - Place your cursor at the top of the wing, press Shift, and drag to the left until the line meets the curve of the wing.

One of the tricks to working with the Pen tool is to try to use as few anchor points as possible; you really only need two to describe any basic curve, such as the arc of this bird’s wing.

Notice that in the back half of the wing, the shape changes somewhat radically. If you attempted to place another point at the bottom of the first wing tip, Illustrator would draw a widely curved path and not the relatively straight line needed. To avoid this undesired result, you need to change the anchor point from a smooth one to a corner. This is done by use of a keyboard modifier and the Pen tool.

Press Alt (Windows) or Option (Mac) and click once on the last anchor point; the Pen tool indicator symbol changes to an inverted V. Note that the left direction handle disappears when the point is clicked.

With one direction handle gone, the path on one side of the point can be curved and the path on the other side, straight. By pressing the Alt/Option key, you’ve temporarily switched the Pen tool’s functionality from drawing to converting anchor points; if you were to click the point a second time, the other direction handle would disappear along with the curved line.

Note: In the Pen tool group, a separate Convert Anchor Point tool is available if you need to apply this functionality consistently.

Now it’s time for you to try the Pen tool on your own. I’ll outline each of the major sections of the image and let you figure out the details on your own.

11 - Use the Pen tool to outline the five tips of the bird’s first wing. Alternate between the low and high points of the tips, in a “valley-peak-valley” sequence. When you’re finished, your path should surround the edge of the wing in a series of diminishing curves.

Next, tackle the second wing. The initial path along the rightmost edge of the wing should require only a single path near the tip. The back part of the wing will require a bit more finesse.

12 - With the Pen tool, outline the second wing completely and end at the base of the tail feathers. Where necessary, press Alt (Windows) or Option (Mac) to temporarily shift to the Convert Anchor Point tool. If you make a mistake when placing an anchor point, you can always press Ctrl+Z (Windows) or Command+Z (Mac) to undo and try again.

13 - Continue outlining the bird’s tail feathers with the Pen tool. When you’re done, outline the bottom portion of the bird, following the contour all the way up to the beak. Move your cursor over the first anchor point until the Pen tool indicator symbol becomes a circle and then click. The path is closed and the stroke is added.

After the path is closed, you’ll notice that the Pen tool’s indicator symbol is once again an X, to show that the Pen tool is ready to create another path.

As you can see in the illustration above, sometimes paths don’t always go where intended. The Direct Selection tool can modify any point’s position or direction handle placement.

14 - From the Tools panel, choose the Direct Selection tool, the white arrow and second icon in the panel. Select any direction handle or anchor point that needs adjustment and click and drag as necessary.

15 - The outline is now complete and fine-tuned. The last action is to fill the path with a color.

16 - In the Tools panel, click Fill. From the Color panel that appears, click the black color swatch all the way to the right of the gradient. Press Ctrl+- (Windows) or Command+- to zoom out until the whole bird is visible. Click once on the JPEG image and press Delete.

All that’s left is to store the file.

Choose File > Save. When the Save As dialog box appears, save the file as bird.ai. When the Illustrator Options dialog box appears, keep the default settings and click OK.

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